For all of his life, billionaire Blake Harrison has firmly believed the route to happiness was keeping his heart free. But after seeing two of his best friends fall hard for women, he’s starting to second guess himself. The problem is, if he can’t get past the second date with a woman, how can he possibly consider settling down? Jokingly, his buddies bet him he can’t go out with the same woman five times. When he gets beaned in the head with a baseball at his team’s practice field, trainer Michelle Stewart is the one to patch him up. His buddies immediately set their sights on the beautiful trainer. She’s the one, they agree. And after a few dates, Blake begins to wonder if she really is… Sure, Michelle is attracted to Blake. He’s sweet and charming and the hottest guy she’s ever dated. But if she’s attracted to him, it’s got to mean he’s wrong for her. For one thing, she works for him. For another, she has a rotten track record when it comes to men, and it’s better if she just steers clear of charming, hot guys. Besides, she has to think about her daughter Mollie and what’s best for her, too. Even though her mind is telling her no, her heart is shouting that Blake is a big yes. The problem is, listening to her heart has always gotten Michelle into trouble. Could it be possible that her heart is finally telling her the truth? Or is Blake just too big a risk?

Billionaire Daniel Trent needs a date for his best friend Grayson’s wedding, but he’s got a bit of a problem. His current closest relationship is with his house sitter, Jackie Stone, who he’s never actually met. Their flirty notes about his beloved tankful of exotic fish are the only fun part of his busy work-only life. When he comes home early after a business trip to find Jackie naked in his bathtub, Daniel is pleasantly surprised to find the woman he likes is absolutely adorable. Grayson, assuming Daniel and Jackie are a couple, suggests Daniel bring her to his wedding. Teasing Daniel over his commitment issues, he even bets that Daniel will end things before the wedding is over. After all, Daniel rarely gets past two dates with any woman. Daniel takes the bet, hoping that Jackie agrees to be his fake girlfriend. The worst thing that could happen is he’ll lose the bet. He certainly won’t lose his heart... Though Jackie agrees to go as Daniel’s wedding date, it turns out the man is the worst boyfriend. Ever. There’s no way they’ll convince anyone at the pre-wedding festivities that they’re a couple. And she really, really wants Daniel to win that bet because he promised to pay for her final year of graduate school if he does. If she wants any chance of that happening, she knows they’ll have to practice acting like a couple, which leads to…the kiss. And then more. Which is bad. The last thing Jackie wants is for this business arrangement to get complicated, and it’s definitely getting complicated. But it’s also getting harder and harder to remind herself that falling for Daniel would be a colossal mistake. A mistake her heart, unfortunately, seems more than willing to make…